Phthalimide → HCID 18972484, compound

Participants

Reaction Steps

1.63 g (1.5 eq.) of phthalimide and 2.91 g (1.5 eq.) of triphenylphosphine were added portionwise while cooling with ice to a solution of 3.0 g (7.40 mmol) of 3,7-dimethoxy-6-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo[b,e][1,4]oxazine-4-methanol in 40 ml of tetrahydrofuran. Then, a solution of 2.06 g (1.6 eq.) of diethyl diazodicarboxylate in 10 ml of tetrahydrofuran was slowly added dropwise at 0° during 2 hours. The reaction mixture was stirred at 0° for 10 hours and then poured into 50 ml of water, 100 ml of hexane, 50 ml of methanol and 50 ml of ethyl acetate. The organic phase was separated, washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated. The residue was chromatographed on 200 g of silica gel with ethyl acetate/hexane (1:1), whereupon 3.61 g (93.7%) of N-[[3,7-dimethoxy-6-[[(2-methoxyethoxy)methoxy]methyl]-10-methyl-10H-dibenzo[b,e][1,4]oxazin-1-yl]methyl]-2,3-dihydro-1H-isoindole-1,3-dione were obtained as an amorphous foam. MS: 534 (M+, 100), 160(8).

Provenance & Evidence